Why is he so insecure about his size?

Our guy guru answers your most pressing sex and love questions.

My boyfriend is great in bed, but he feels really insecure about the small size of his member. I've told him again and again just how amazing he is and that I'm more than satisfied, but he doesn't seem to buy it. What else can I do to reassure him?

Size might not matter to you, but it's a huge deal to your boyfriend, especially when his, um, package, isn't all that huge. It's great that you're telling him how amazing he is and all, but I wonder exactly how you're putting it. My concern is, you might be saying stuff like "It's not the size of the boat, it's the motion of the ocean" or "I love your little friend; it's just so cute." As a general rule, any reference to his size is a major no-no. It's kind of like him trying to talk to you about your weight  better not to even go there at all. He's probably so massively self-conscious about his small size that there's very little you can say to convince him that it's not an issue. My advice: Instead of telling him what a great lover he is, you should actually show him how much you love his bedroom prowess. Moaning, gasping, back clawing, and spontaneous bone jumping say a lot more than just "Wow, that was great." Next time you catch him obsessing over his teeny weenie, just blow it off with an eye roll and a line like "Whatever, dude. You know you're awesome in the sack." If you act like his size never even crosses your mind, he should stop harping on it as well.